


Adventures with Olicity

by Dani1995



Category: Arrow (TV 2012)
Genre: F/M
Language: English
Status: In-Progress
Published: 2016-03-28
Updated: 2016-03-28
Packaged: 2018-05-29 17:59:43
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 7
Words: 8,529
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6386584
Author URL: https://archiveofourown.org/users/Dani1995/pseuds/Dani1995
Summary: <blockquote class="userstuff">
              <p>Collection of short one shots that I've written about Oliver and Felicity and different things that happen in their lives.</p>
            </blockquote>





	1. Of Ex-Girlfriends and New Girlfriends

**Author's Note:**

> This will be a collection of all the one-shots I write about Oliver and Felicity! They are not set in a particular verse, they are just all AU's that I've thought of. I also accept prompts! Send them to me on tumblr (lovewillsurviveallobstacles.tumblr.com) or on here :)
> 
> First chapter, prompt by anon: Oliver runs into a crazy ex-gf and makes Felicity pretend to be his gf. 
> 
> A/N: So I thought I’d finally tackle this prompt.. it has been quite a while since I’ve written something, and I have been really stressed lately since I don’t know if I can continue into the second year of my study.. so this is to relieve some stress, and I still had it in my prompts list.

It started out in the lair. Oliver and Felicity had been spending more time together there, but since a short time ago they also started meeting outside the lair. This didn’t really happen before, so it was a little weird in the start, but soon they became even closer. They started going out for coffee, and when Oliver needed some new business suits because he got back QC and needed to appear fresh, Felicity offered to go with him to shop. Their ‘dates’ usually went the same. They got some coffee or lunch, and then they did what they had to do.  
While enjoying their lunch together, they talked about small things, and just enjoyed each other’s company. After they had finished, they went to the dress shop were Oliver always got his suits. They had everything and more, and they also adjusted the suits after you bought them, so they fit perfectly. It really was the best shop to go to.

As soon as they stepped inside they were helped by a really nice woman. She knew exactly what was appropriate at the moment as far as suits go, and she really had an eye for what suited Oliver and what didn’t. Everything went smoothly, the saleswoman showed them some suits, and Felicity mostly decided which one she liked and which ones she didn’t like. Oliver had some say as well, of course, but he knew that Felicity knew what he liked, so he just let it be. 

They had picked out four suits for Oliver to try on, and as he went in to the changing room, Felicity looked around for new ties, and some dress shirts for him. When he had the suit on, he came out to show it to Felicity, and she whistled appreciatively. “Looks good, Oliver!” she said, and the saleswoman agreed. Then he heard someone say: “Ollie? Is that you?” 

“Shit”, he thought, and almost ran to Felicity’s side. “Please pretend to be my girlfriend right now, I’ll explain later okay?”  
Felicity knew Oliver had a lot of exes. She also knew not all of them were sane. I mean, after meeting Helena, she could safely say some were certifiably crazy. So it wasn’t really a surprise when Oliver did this, but she still wondered why. She nodded anyway and Oliver turned around and said: “Alyssa, I haven’t seen you in a long time. How are you?”

“OMG it IS you,” the other woman, apparently named Alyssa, screamed. “I missed you so much Ollie! I can’t believe I’m running into you here!”

Oliver came even closer to Felicity, if that was even possible, and said pointedly: “Alyssa, this is my girlfriend, Felicity.” 

Immediately the woman’s behaviour changed, and she almost hissed. “So you’ve moved on then? You didn’t think of me anymore, at all? After all these time, I still love you, and you just have someone else by your side? I can’t believe it.”

Felicity was stunned. She didn’t even know the woman, so clearly it had been a long time since she and Oliver had a relationship. And here she was acting like it was a recent break up and Oliver should still be hung up on her. 

She calmly stated: “Well, Oliver is happy with me now, so if you’re done screaming at him, you can just leave, please, and let us do our shopping.”  
Suddenly, as if to prove a point, she kissed him on his cheek, near the corner of his mouth. Oliver stood shocked, frozen in place, and Alyssa just ran off steaming. 

“OMG how could you have even dated her? She is the craziest one yet! When did you date her, why is she acting like this is a recent breakup?” Felicity ran through her questions at the speed of a runaway train.

“I know, I didn’t know I’d ever run into her again, she used to live on the other coast? But I dated her like 3 years before the island, and she was even the one to break up with me. Guess I’m interesting again now that I gained QC back..” Oliver stammered. 

“Well, you’re lucky you had me with you, you probably wouldn’t have survived on your own.”

~*~*~*~*~*~*~*~*~*~*~*~*~

After that afternoon, they not only came back to the lair with a bunch of new suits, they also came back with a whole new tension between them.

Whenever Oliver would touch her, she would feel the urge to shiver (which she mostly tried to suppress, because Oliver wouldn’t be interested in her in that way) but his touches also became a lot more frequent, which made it really hard not to show anything.

Oliver wasn’t unaffected by what happened either. He had seen a quick flash of what a relationship with Felicity could be like, and he just couldn’t let it go. But on the other side, he knew it wasn’t really possible to have a relationship with Felicity. It would be too dangerous for her. So he settled for being near her, and being able to touch her like he normally did.

~*~*~*~*~*~*~*~*~*~*~*~*~

One evening, when Diggle couldn’t stand the tension anymore, he decided to say something to Oliver.  
“When are you going to do something about the tension between you and Felicity? You two have been circling around each other even worse since the afternoon you went on that suit shopping trip. What happened? And why are you not doing anything about it?”

“I don’t want to hurt her Digg, or put her in more danger than she already is. It’s probably safer for her if we’re just friends.”

“You do know that all those times you spent together were basically dates too? Just without the label on them, and just as friends? She wasn’t in anymore danger then.” Digg decided to leave it at that. He could see he had given Oliver something to think about, and he was glad he did. Those two should just give in already. He could see how Oliver looked at her just now, during their conversation, while she was working at her computers, and how Felicity looked at him when she thought no one was looking.

Oliver just realized Digg did have a point. How many lunches and shopping trips and movie nights had they had already as friends, and nothing worse had happened to her? Did he want to keep himself away from her any longer? He had some serious thinking to do. Before he could though, Digg said he would be getting them food, and went up the stairs. That left Felicity and Oliver alone.

“Oliver” Felicity started. “I’ve decided that you don’t get to dictate our relationship. I know you feel something, because you’ve been touching me all week, no, I don’t mean touching in that way, just that you’ve been touching me more than you usually do, and I can’t really handle that anymore, I mean, I love you being affectionate, but it just does things to me, and I can’t really explain, I also don’t think you really needed to know that, but to the point, if you want to really date me, just say so, or stop messing with my feelings.” She was still turned to the computers with her face, so she didn’t see Oliver getting closer, until she felt him turning her chair around. 

“Felicity. I just decided I didn’t want to wait any longer. I keep thinking of you, and I want our dates to be real dates, not friend dates. I want to kiss you when I want to. I want to hold you when I want to. I want to touch you where I want to. I want to wake up next to you. I want everything.”

“Well, kiss me then, you idiot” she told him, and he complied. 

From the stairs, Digg looked on, said to himself: “That was about time.. couldn’t have handled the tension for much longer.” and went out the door to get them some food. Things would hopefully change in a good way for once, for team Arrow.


	2. Frustration During Office Hours

**Summary for the Chapter:**

> Prompt from lostforsoul on Tumblr: It would be nice to write about a normal day at the office Felicity’s POV and Oliver a reunion with Isabel and how frustrated and annoyed both Felicity and Oliver are.

Felicity hadn’t expected to feel this way. She knew Oliver didn’t feel anything for Isabel, and that she had no right to even feel like she was jealous because she wasn’t dating Oliver or anything, yet when his business partner had requested a private meeting, and adding that private meant his EA couldn’t come either, she couldn’t help but feel slightly threatened by the woman. Up to that moment, the day had been completely normal. She had come in this morning with a serious lack of sleep, like always (2 jobs, quite a hassle), but perfectly on time unlike her boss who was seriously always late!

When he came in, she had informed him of the meetings he had that day, which also included the one with Isabel, told him to grab his own cup of coffee after he tried to make her get one for him, and basically started working. She still didn’t think she was actually very good at being an EA, but she liked that while having that cover she could run searches and research for her other job, the one causing her that serious lack of sleep.   
Now Oliver was in that meeting with Isabel, and she just really needed to tell him about something she’d found, and he was not available. This would have so much easier had she just been allowed to join in the meeting. Normally, because she had to be able to reach him with Arrow business all the time, even when he was busy, she went with him to the business meetings. Okay, it was also a bit for when he got bored and she needed to keep him focussed. But since Isabel specifically required her not to be there, she couldn’t this time. 

She didn’t know why Isabel didn’t want her there. It wasn’t like she should feel threatened by Felicity. She was just an EA after all, and she was preeeetty sure Oliver didn’t feel the way she felt about him. So no need for Isabel to feel threatened! Although she didn’t know why the woman thought she even stood a chance. Oliver made it quite clear after Russia that nothing was gonna happen again, by ignoring her as much as was socially acceptable.   
Felicity actually started to get annoyed at herself now. Why was she even thinking about this? It was not like she stood a chance either. She couldn’t allow herself to get frustrated over Isabel trying to get Oliver. She just needed to focus on her job, because Oliver wouldn’t think of her any other way than a friend, or a trusty IT sidekick. She definitely needed to move on she thought to herself. 

Meanwhile though, in the conference room, Oliver sat in his meeting with Isabel, and he wondered if she saw he was totally not paying attention. He was bored out of his mind, and Isabel just rambled of numbers, and what they still needed to do to reinforce the company’s good name. It just didn’t interest him at all. He should have had Felicity here; she could have helped him stay focused. Though she was a distraction all by herself. Not that she noticed she distracted him. She shouldn’t. Because he couldn’t think of her other than a friend. That could get her in some serious danger. The fact that his body didn’t seem to get that frustrated him. He couldn’t stop thinking of her, and the way she distracted him should be illegal. All her little mannerisms intrigued him to no end, and he couldn’t help but watch her when she was in the same room as him.   
All these thoughts were suddenly cleared from his mind when he was shocked into reality by Isabel asking him if they maybe could get a coffee together once. After all, they’d discovered in Russia they actually had quite some things in common, and maybe they could just spend time outside of work with each other. You could definitely say he was surprised by this, and actually quite annoyed. Was this the reason she didn’t want Felicity in this meeting? She actually had intended to ask him out? He quickly shut her down, but still trying not to hurt her feelings by saying they shouldn’t, because they had to work together so closely, and it was probably not a good idea. Though the real reason was that, although he couldn’t start a relationship with Felicity, it also didn’t feel right to go out with someone else. His feelings for his EA were seriously getting out of hand, he thought to himself, frustrated.


	3. Finally

**Summary for the Chapter:**

> Prompt: Laurel is tired of the dance that is Oliver & Felicity. She wants them to have the happiness she has found, so she takes matters into her own hands. (By heatherdani85)

**Notes for the Chapter:**

> so this is the first prompt I have filled for the prompts I got! Slightly AU, but just on the important stuff (like the Sara and Tommy front). I hope you like it, and please review if you have time!

Having once been the object of Oliver’s affection, she could tell with certainty when he was truly in love and when he wasn’t. She had noticed him falling in love with her, and falling out of it. She saw the girls he had been with, and knew he might have liked some of them, but he was never in love. 

Unless he was with Felicity. She didn’t know the IT-expert that well, but she knew that Oliver was totally and irrevocably in love with the girl. Whenever he was around her, he smiled just a little wider, his eyes were a little brighter; he just seemed more comfortable with himself. 

Which is why it was all the more frustrating that he wasn’t doing anything about it. That he wouldn’t let himself be happy. She had moved on after Oliver, and now was living happily with Tommy. Oliver just had had the string of one night stands, up until he realized he was in love with Felicity, then those stopped too.

But he never told her how he felt. He never let her see his true feelings. Whenever he came close, he just shut it down. She could see it on his face, and it was a shame. He would be so much happier if he just gave in. But he convinced himself that he wasn’t good enough for Felicity. And nothing could change his mind. Every time Felicity was in danger, it just proved to Oliver that she was better off without him. 

Meanwhile, she could see that Felicity wasn’t happy either. She tried to live her life to the fullest, and had tried dating that other guy, Ray, but that turned out to be nothing. Or rather, Felicity realized she couldn’t be with anyone else the way they deserved someone if she was still in love with Oliver. So she broke it off with Ray.

So they were both basically living unhappily and apart, and Laurel had had enough of it. She decided to take matters in her own hands, and arranged for Thea to help her. The girl had seen Oliver and Felicity dancing around each other for long enough and agreed with Laurel that it had been enough, they had to make Oliver and Felicity see some sense. So they fabricated a plan.

Thea would go to Felicity and talk to her, about life, and the intention was about Oliver. Thea and Felicity had become quite close lately, and they talked about a lot, but never about Oliver. It was sort of a taboo topic, so to say.   
Then they would somehow get Oliver to overhear their conversation, and how Felicity felt about him. Hearing it out loud might help trigger him to act on his feelings. Then again, he already knew how Felicity felt about him, so it might not help at all. But Laurel and Thea both thought it was worth a try. 

The plan really went off without a hitch. Felicity and Thea met up at a trendy bar in the city, and while enjoying a glass of wine they talked freely, and when the topic of Oliver came up, they just continued the conversation. Felicity didn’t even hesitate to tell Thea all about how she felt, and how hurt she was that Oliver didn’t want to give them a try. After everything that they had been through together, why would he not trust her enough to go through this together? She was in danger anyway, so that argument was off the table. All the bad guys knew she was working with the Arrow anyway? So there shouldn’t be a problem really.

Laurel had managed to get Oliver to the bar just in time. She sent him to get them some drinks, and he had to pass Thea and Felicity’s table to do that. He passed by and he immediately noticed they were talking about him. They hadn’t seen him yet, so he stayed at the bar just a little longer. What he heard opened his eyes.

Suddenly he realized he wasn’t just hurting himself with his actions, but he was also hurting Felicity. By denying himself happiness, he had also denied her happiness. She had not been able to move on because he had kept dangling maybes while never committing himself fully to her. He walked over to the table and said: “Can I please speak to Felicity for a moment please, Thea?”

“Oliver? What are you doing here?” Felicity asked, afraid that he overheard their conversation, and decided to once and for all get clarity on the issue. 

“I wanted to talk to you Felicity.” Oliver said. “I know that I’ve been different lately, and that I’ve been leading you on, and I’m so sorry for that. I know you deserve more, and I know that I’ve always said I might not be the best person for that, but I want to try, Felicity, I want to try, for you, because I love you, and I want to be with you, and I can’t deny myself, or you, that anymore. We’ve been dancing around each other for so long, and I know it’s mostly because of me, but I’m done dancing alone Felicity. I want to be dancing with you.”

Felicity was stunned. Never had she heard such a speech from Oliver. She almost felt like she was dreaming. Never had she expected to hear those words from him. She didn’t know to answer to this waterfall of words. She had never been lost for words, but now she was.   
So she did the next thing she could think of. 

She kissed him.


	4. Bookstore AU

**Summary for the Chapter:**

> Bookstore AU I wrote for befitandchase :)

It seems like he was always there if she was there too. She’d be browsing a book, and he’d turn up behind her, or on the other end of the isle. She never stayed for long, the bookstore was more of a regular stop on her walk home from college. She’d stop by the bookstore, and she’d browse the new books. Sometimes she just grabbed a book of one of the worn shelves and read it in the little cafe the store also had.   
She loved the little store. It was a very old building, but the fact that the shop looked a little worn gave it a certain charm. It always smelled like books and coffee inside, and she could easily spend an entire afternoon there without noticing the time passing. She guessed the same went for the stranger that seemed to turn up next to her so often. 

She had to admit that she had noticed him sneaking glances while she was browsing or reading, but she didn’t really mind. He was quite attractive, and as long as it didn’t turn into another one of the stalker fiasco’s she had experienced in her first year, she liked the attention. She had often sneaked a look at him too, and had sort of kept track when he seemed to turn up. If she went to the store immediately after class on Tuesdays and Thursdays, he was often there as well. He always seemed to either be there just before her, and when she came in he would look at the door and give her a little smile. 

One day, when she walked into the bookstore, she didn’t look around for him. She’d had a really long and terrible day in class. The class ran long, and they had to do an assignment that no one really understood and was way above their level. When she had grabbed her favorite book of the shelf and went to sit down with her coffee to drown herself in another world, he suddenly stood beside her, a smile on his face, and said: “I noticed you looking down on your way in, can I buy you the next coffee?”

“Sure”, she answered, “I’m just not really enjoyable company today, I’ve had a horrible day.” 

“That’s okay.” He said. “Have you read this? It always makes me feel better when I’ve had a terrible day.”

Before she knew it they were caught in an intense discussion about favorite books, and childhood favourites. Another coffee was bought, as promised, by him, and then another. They didn’t just talk about books after a while, but discussed family, holidays they’d been on, high school memories. Before she knew it, so much time had passed that her roommate rang her to see where she was. She knew she had to go home then, but she didn’t really want to. She’d never had such an amazing conversation with someone, and they didn’t even know each other’s names!

“I really have to go” she said with a sigh. “My roommate is already wondering where I am, and it’s getting really late.”

“What’s your name?” he said. “I really enjoyed our conversation, and I really wanna do it again, if you’d let me.” He asked shyly. “I’m Oliver by the way.” He added, more as an afterthought. 

“I’m Felicity.” She answered, the corners of her mouth rising in a slight smile. “I’d really like to meet you again, let me just give you my number, and just give me a call whenever.”

After that, they parted ways.

When she got a call from an unknown number the next day, picked up the phone, and heard a familiar voice, she had never smiled bigger.


	5. Blind Dates and Confessions

**Summary for the Chapter:**

> Prompt: Felicity on a date but not with Oliver. (By a guest on ff.net)

So, it was safe to say Felicity’s social life lacked colour at the moment. Between working a day job and a night job for Oliver Queen, and keeping up with the newest tech news, she didn’t exactly have time to go out. Her friends, whom she did manage to meet almost every week, always complained that she didn’t get enough free time. And sure, she didn’t. But she didn’t exactly mind. But sometimes, when she noticed Oliver had yet another date, and she didn’t get the time to actually even meet new people, she couldn’t help but feel jealous. Not of the woman Oliver dated (though she wouldn’t deny that played a part), but just that he had the time, and she didn’t. 

Which is how she ended up here. During one of the weekly get togethers with her friends they had decided she needed to date someone again. And they didn’t care whether she approved or not, they would set her up with someone, since she apparently didn’t have the time to meet someone. And she liked that they cared for her so much, sure, but sometimes they could be a bit overbearing? And form past experiences, blind dates usually didn’t go very well for her. Either the guys couldn’t handle her constant babbling which she did when she was nervous (and you bet she was nervous for these blind dates), or they were just plain boring and they couldn’t keep her attention. And then of course there were the guys that only thought she was pretty, and were interested in her for only one thing. Those guys usually didn’t work out either. So yes, she would say she was apprehensive for this blind date when she was set up. But when she got the message she had to be at her favourite Italian restaurant, which was just around the corner from her house, this Thursday, she did get kind of excited. It had been a long time since she had been on a date, and she liked the process of getting dressed up for one. When she broke the news to Oliver, that she couldn’t be in this Thursday, he put up a bit of a fight at first, but when she made clear that she deserved a night off every once in a while too, he agreed. Not that he could have kept her from going. He might be her boss, but he definitely wasn’t the boss of her. 

When she arrived at Notte Stellata, she was wearing one of her favourite dresses, paired with some gorgeous shoes. She had kept her hair simple, just letting it fall as it naturally would. And she was actually excited, because this was her first real night out in a while. She walked in to the restaurant, and immediately someone stood up and walked towards her. “Felicity Smoak?” he asked. When she nodded in confirmation, he said: “Hi, I’m Aiden. Aiden Flanagan. Let’s walk to our table shall we?” As she followed him to the table, she couldn’t help but notice that he was quite handsome, and that he certainly was well built. Though not as well built as Oliver of course, but well, not everyone had spent 5 years on an island and built up muscle. Wait, why was she thinking of Oliver? She was on a date for god’s sake. “You look beautiful” Aiden said to her when they were seated. “Thank you!” Felicity said. “Did my friends tip you off or something, because this is actually my favourite restaurant, and you wouldn’t know that, unless of course you asked around about me, which is totally understandable because blind dates can be kind of scary I guess.. I mean I wouldn’t put it against you if you wanted to know who you were going to deal with before you went out on a date with them, though it’s also kind of strange, to ask around first..” “Felicity” Aiden interrupted her. “I didn’t actually ask around, though I did hear from your friends you had the tendency to babble when nervous, which I guess is what you’re doing now. This is actually one of my favourite restaurants as well, so that’s a complete coincidence! Though I’m very glad you like it.”   
Felicity was kind of flustered. Why couldn’t she ever stop the stupid babbling? Though he didn’t seem like he minded too much, he had just interrupted her. “If you think I’m going off on a babble, you should just stop me” she told him, “I wouldn’t want to annoy you with my incessant talking.”   
“I really like you babbling though, it makes you honest.” Aiden answered. 

That was the first time any guy, except for Oliver and Diggle who just laughed at her when she was babbling most of the time, didn’t find her babbling annoying. She was surprised, and she voiced that to Aiden as well. But he really didn’t seem to mind. This made her so much more relaxed, and she was able to just enjoy the date. He was really interesting, and they could actually have a really nice conversation, she found out. Also, he wasn’t too bad to look at. In fact, he was quite handsome. Her friends had really done well this time! 

Dinner flew by, and before they knew it they had been talking for hours, and it was getting near to midnight. Though she’d gotten the night off, she did have to work in the morning, and so had Aiden. She found out he worked as a veterinarian, with his own clinic in the city, so he often made long days. He insisted on walking her home, even when she was only 2 blocks away from her apartment building. When they arrived, he was very polite, and kissed her on the cheek, which made her blush. “I really enjoyed tonight Aiden,” she said. “I hope we can do this again sometime, just call me.” He affirmed this and walked off into the night, since he didn’t live to far from here either he didn’t go by car. When she went inside, she felt the nice glow you get when a first date goes well. Like you could maybe really like the guy but you’re not really sure yet? That feeling. She certainly had an enjoyable evening though, and she wouldn’t mind repeating it another night. She fell asleep with a smile on her face that night. 

The next day was more than normal. Oliver didn’t mention last night, so she assumed nothing special happened in the lair while she was gone. So she worked through the day, and when she was done at QC, she went to Verdant, well, technically the basement under Verdant. She still had the nice glowy feeling from last night, and today had been a good day as well, so nothing had diminished that glow. When Oliver arrived at the lair somewhat later than her, he said: “You look like you had a good night yesterday. You seem happier.” Felicity answered: “Yeah, I actually had a really nice date yesterday. I was set up on a blind date by my friends, and usually those don’t end well, because well, those guys don’t normally match me? But I was actually pleasantly surprised yesterday, and you didn’t want to know all that...” she trailed off, seeing Oliver’s eyes had kind of glazed over. “Well, I’m glad you enjoyed your night off Felicity, but I would like to get back to catching the bad guys now, if you don’t mind.” Oliver said shortly. Felicity couldn’t help but feel bothered, by how he acted. Was he not going to approve now? It wasn’t like she was out with a different guy every week, like he was with girls most of the time. He didn’t get to feel, dare she say it, jealous? No, he totally didn’t like her that way, personally proved by him taking out a different girl each week. 

So when she got a call from Aiden the next day, asking her if she wanted to maybe go see a movie tonight, she quickly agreed, and told Oliver she wouldn’t be in that night. He sourly agreed, but he didn’t seem to like it very much, Felicity thought. Well, bad luck for him. She was going to have fun. When she got to the cinema, she was surprised to find Aiden had picked to see Frozen, the new Disney film. She really had wanted to see that, and apparently so did he. They had lots of fun, and the movie was amazing, both fun and heartbreaking at moments. After the movie, they had a drink, and talked some more. She was really delighted they could talk so well to each other, and conversation flowed easily. When it was time to go home, he dropped her off at her apartment building, just like the first time, but this time he didn’t kiss her cheek. He left a chaste kiss on her lips, which left her dumbfounded for a moment, but after a second she kissed him back. She didn’t let it go too far though, she wasn’t planning on sleeping with him after the second date, though he certainly didn’t seem to mind kissing her, and she really enjoyed kissing him too. There were definitely sparks, she thought after she went upstairs and he went home. Which was good, because then maybe she could finally forget about her stupid crush on Oliver, which he obviously didn’t return. 

Their third date took place at her house. And yeah, she knew how that looked. But honestly, they were just watching movies and eating popcorn. Okay, and maybe cuddling, and making out a bit. But nothing more than that! Throughout the night though, Oliver kept calling her, though she had clearly told him she wouldn’t be available. After the umpteenth time he called her phone, she just turned it off. He had to accept she had a life of her own too. She didn’t expect him to turn up on her doorstep because she didn’t respond to the calls.

When she opened the door after the knock and saw him standing there, she got agitated. “Oliver, you can’t just show up every time I don’t answer my phone, I told you I wouldn’t be available tonight. You have to respect I have a life of my own too, I can’t just show up at your beck and call!”   
“Who is it Felicity?” she heard Aiden shout from inside, where he was still sitting on the couch, waiting for her to come back, and she flinched. Oliver probably wouldn’t react well to her bailing on a night of helping him as the Arrow, to spend it with a guy watching TV. But she could do what she wanted, and he couldn’t order her around. “Oh, you’re on a date?” he asked. “Yes I am, now, can you please get off my doorstep, and let me get back to my date?” she said, frustrated. “Ye-uhm.. Yeah, of course, I’ll see you tomorrow then.” And he walked to the stairs. She closed the door and went back to the living room. “Who was it?” Aiden asked. “Oh, just my boss, who thought he could just knock on my door late in the evening and expect me to help him, while I obviously told him I wouldn’t be available tonight.” Felicity answered, still frustrated. Why would he even come over? She had told him he couldn’t come to her for help tonight, and yet when she didn’t answer her phone he still came over like an overbearing mother bear that couldn’t live without knowing where she was every second. The thought of Oliver as a mother bear made her giggle slightly. But she turned her attention back to Aiden, and they continued the movie they were watching as if nothing happened.

The next day though, Oliver was sulking. She could definitely call it that. She didn’t even know why. It wasn’t like she hurt him or anything; she just told him the truth. But he still seemed really hurt. So later, when they were in the lair, and Diggle wasn’t there yet, she asked him what his problem was. She totally didn’t expect what came out of his mouth though. He told her: “You know what my problem is Felicity? My problem is that even though I shouldn’t care too much about you, I do. I didn’t know seeing you with another man would be this hard! Another man who makes you happy, like I can’t, another man for you to talk to about your day, another man for you to seek comfort from! I love you, and I can’t help it, but I want you to be happy, and you couldn’t be that with me. I couldn’t give you the life you deserve, and Aiden obviously can. He is normal, and he is good for you, and you clearly like him. So, I’m not okay. Because I love you. And I don’t know if I can handle seeing you with someone else.” She was stunned. First of all, because Oliver usually wasn’t this outspoken about his feelings. Second of all, because did he just admit he loved her? What? She couldn’t actually form a response to this outburst of emotions he just gave her. So she did the one thing that seemed logical to her right now: she kissed him. At first he was not responding, obviously not expecting her to react that way. But after a few seconds, he started kissing her back. One of his hands went to the back of her head and the other went around her waist to pull her closer. His tongue slightly licked at her lips, asking for access, which she gratefully allowed. 

When they pulled back, they were both slightly out of breath. “I guess I have to break it off with Aiden then.” Felicity quipped. “Cause you might not have known, but I’ve had a crush on you which turned into more later since you walked in with the laptop full of bullet holes. And you might not have noticed, but that attraction never went away, and I love you too, I just never thought you could love an IT-girl like me, I mean, I’m obviously not really your type, and well, I just never expected this to happen-“Oliver gave her another kiss. “Shut up, Felicity” he said, laughing and she agreed, kissing him again.

**Notes for the Chapter:**

> Felicity’s first date outfit: en.paperblog.com/first-date-outfit-3-the-dinner-date-273165/


	6. A Tale of Stores and Shopping

**Summary for the Chapter:**

> Prompt (by ladybuglloyd on Tumblr): Oliver has to buy Felicity something for a mission because she doesn’t have time but he has no idea what she likes. He ends up buying the wrong thing or has an uncomfortable time shopping in a women's store.

**Notes for the Chapter:**

> I didn’t completely follow the prompt, but this just escaped from me. The next chapter is the story which does follow the prompt! Also, please leave a review of some kind, because I’d love to know what I could improve on my writing.

When Oliver invited Felicity to come along to a charity gala he had to attend, he hadn’t expected this to happen. He had expected her to freak out when he specified it wasn’t as his EA, but as his ‘date’ date, and that did happen. But when she told him that she didn’t have time to shop, and that he would have to buy something for her to wear, he was the one to freak out. Which was unsurprising to say the least. He didn’t have any idea what to shop for a woman! What she needed, or what she wanted, or what colour she wanted... He had no idea at all. Normally he’d go to Thea for advice, but she was so busy with Verdant that she wasn’t able to help him. 

That’s how he ended up here, in a dress shop, with no idea what to buy. He had a general idea of the colour (green, because he loved seeing her in a colour that represented him in a way), and of the style he wanted, and of course he knew her size, because she told him that when she told him he had to buy her a dress. That conversation was accompanied by a lot of babbling actually. He had to buy her the dress, but of course he wouldn’t have to pay for it, she would pay him back, and she would need underwear too, but he didn’t have to buy that she would do that herself. Oh and jewellery, no, that wasn’t a hint, she could take care of it herself. But Oliver had assured her that he would of course pay for her dress, that wasn’t a problem, he asked her to go with him of course. If she wanted to, he could buy her underwear as well, and jewellery he would certainly take care of, no questions asked. But Felicity insisted (accompanied by another babble) that she would buy her own underwear, because that would be waaaay too awkward, if he were to buy it. 

And now that he was in the dress shop, he was glad she had insisted. Because he found it hard enough to pick out a dress as it was, let alone he had to have bought her underwear. He wouldn’t have had a clue! The assistant had already asked him if he needed any help, and he said he was looking for a very special dress, preferably emerald, and it had to be long as well. The price didn’t matter to him, as long as it was special, he said, and she had went to pick out some dresses which he could consider. 

When he finally found a beautiful special dress he liked, and which he thought would make Felicity look amazing (which she always did in his opinion, but well, this would make heads turn), he decided to go the family vault to look for some jewellery to accompany this dress.  
After he had spend another hour at least looking for jewellery, he had finally found some pieces he really liked, and wouldn’t overwhelm Felicity too much. 

The next day, he decided to ship the dress to Felicity’s desk, so she would have a surprise during her working day. Also, this granted him the opportunity to see her first reaction, since his office walls were made out of glass. When the package arrived, he saw her first reaction was surprise, as she noticed the package was for her. Then it was amazement when she opened it and saw the dress, the shoes which went with it, and the jewellery he had chosen to accompany it with. And then there was the furious, though thankful and happy look she sent him. The furious look because she didn’t want to be spoiled by him, the thankful and happy look, well, for obvious reasons.  
He went over to her desk and asked her: ‘Did I do well?’ When his question was answered with a very wide smile, he knew her answer. 

****

When he saw her walking down the stairs of her apartment building that evening, when he came to pick her up, he was amazed by how beautiful she looked. The dress fit perfectly, and while he didn’t particularly enjoy shopping for it, he loved how she looked in it. He greeted her with a peck on her lips, at which she sucked in a breath, and he saw the look of surprise on her face. But he told her: “I told you you were going to be my ‘date’ date for the evening, and I plan to enjoy every second of it. And if you want to, I want to enjoy more evenings like this. I really enjoy spending time with you Felicity and you look beautiful tonight, every day and every night actually, and I would love to spend more of those days and nights with you, if you’d let me.” She replied by giving him a kiss.

**Notes for the Chapter:**

> Felicity’s dress: http://www.aliexpress.com/item/Free-Shipping-Cost-2012-Vnaix-P0014-New-Arrival-One-Strap-Long-Sheer-Chiffon-Emerald-Green-Prom/558775648.html


	7. A Mission Oliver Never Planned

**Summary for the Chapter:**

> Prompt: Oliver has to buy Felicity something for a mission because she doesn’t have time but he has no idea what she likes. He ends up buying the wrong thing or has an uncomfortable time shopping in a women's store. (by ladybuglloyd)

**Notes for the Chapter:**

> So this is the story that does fill the prompt, instead of the gone off the rails story written the other day. I might write a sequel to this which includes the mission, but I’m not sure yet. Kinda depends on the response for this story. Anyway, I hope you’ll enjoy this story, and don’t forget to leave a review! This isn’t beta’d, so if you see any mistakes, please point them out to me. Also, if you’ve got any tips for me to improve my writing, please share! Now, enjoy the story.

When Oliver planned the mission, he hadn’t planned to have Felicity on the field at first. But when it came apparent that she would have to be in the field, because they couldn’t do this mission without her, he easily yielded. Both Diggle and Felicity were surprised it was this easy to get him to let her in the field, but hey, they weren’t going to complain about an easy victory. When she got to know what the mission actually included, and why they would need her, she was a bit apprehensive at first. 

The plan was to infiltrate a quite seedy bar/club sort of thingy, and Oliver knew he couldn’t be seen there. Diggle wouldn’t have much of a chance getting in (“no offense”, Oliver said, “but getting a girl in would be so much easier.”) Which is how the choice fell on Felicity. In the bar they were infiltrating, drugs were being traded, and it was Felicity’s task to be bait, sort of. She would have to pretend to be interested in buying the drugs, and then Oliver and Diggle could take out the dealer after getting a description from Felicity.   
But none of the member of team Arrow had thought about the appropriate attire needed for this mission. And when they thought of it, there was only a day left before the mission was supposed to go off. 

“Well, Oliver, we should have thought about this earlier then, shouldn’t we? Now there is no time for me to go buy something that wouldn’t stand out in the club, and the whole mission will have to be moved, all because we didn’t think of the clothes I should be wearing!” Felicity said, almost using her Loud Voice. She was clearly angry that they missed this minor detail. But Oliver had already thought of a solution. “I can go buy you something you can wear, no worries. I got time enough.” “You do know what kind of clothes I’m gonna need, right Oliver?” Felicity asked incredulously. “All the girls in this club/bar whatever it is, are going to be dressed for getting attention, which means sexy and showing lots of skin, which I’m not completely comfortable with anyway, and if you have to buy me these clothes I’m gonna be even more uncomfortable, let alone you. No, we’ll just have to move the mission up, so I’m gonna have time to buy clothes and there won’t be any trouble, you can’t just buy me slutty clothes, if I’m gonna be dressed like that, I prefer to pick out my clothes by myself, thank you very much.”  
Oliver just looked at her, and she sighed. “Okay, so there isn’t actually an option to move the mission? I’m just gonna have to let you buy me these clothes? Well, fine, but just remember you insisted when you are uncomfortable and feeling out of place in the woman’s shop. I WARNED YOU!”  
OQOQOQOQOQOQ

Now that Oliver thought back to that conversation, he wished he had listened to Felicity. He was standing in the middle of a store, and he had no idea what to buy. He didn’t even have the slightest inclination of what Felicity would still find acceptable, and what would be absolutely crossing the line. He did feel very relieved that he wouldn’t have to buy her underwear or lingerie, because God, that would have been at least twice as embarrassing as what he had to do now. He had no fucking clue what to buy now, let alone if he would have had to buy that! Well, he might have imagined her in lingerie a few times, but that was different! He didn’t know what she liked to wear; he just knew what he liked her to wear.   
But that was not the problem he had right now. He had to buy Felicity something sexy, but not too sexy, something she would still feel comfortable in. While she regularly wore dresses and skirts as his EA, that was not something that would work for this mission. Those dresses, “though sexy”, he thought, “How could she think she would not be able to pull off a sexy dress? She did it all the time in his opinion”, were still office appropriate. The dress she had to wear tonight couldn’t really be office appropriate. He knew she didn’t like it, but he didn’t like it either. “I’m really confusing myself today” he thought. He had never thought of Felicity like that, okay, maybe he had sometimes, but he had never allowed it to lead anywhere. He couldn’t burden her like that. She would be in immediate danger were she to be associated with the Arrow, especially if it was romantic. 

“Focus on the mission Oliver” he thought to himself. This mission was to buy Felicity something scandalous. Since he had by now scouted the racks for over half an hour and still hadn’t found anything he deemed fit, he decided to ask a saleswoman for help. He wasn’t used to asking for help, but in this case, he had no other choice. He wasn’t going to find anything for Felicity otherwise.   
Luckily, he just had to buy her a dress, and no accessories, because if he had to buy her shoes and jewellery as well, he probably wouldn’t have gotten it done in one day. He had to admit, shopping for women was harder than it looked.   
“Excuse me, miss” he asked the saleswoman, “I need to find a dress for a friend, but I can’t find anything I think is fit for the situation in which it is needed. Would you be able to help me?” “Mister Queen!” The saleswoman said, surprised to see him in the shop. That would be his luck, being recognized while buying a sexy dress for a woman. The press was going to have a field day if they found out. Now he was even more uncomfortable. “Of course I’ll help you, what are you looking for exactly?” Okay, so now he had to correctly explain to the woman that he needed a sexy dress, but that would make it look like he was buying something for a girlfriend probably, and that he was only doing a favour for himself! Which was totally not the case! Well, he simply had to deal with it, it wasn’t like he wasn’t used to awkward situations.  
“I’m looking for a dress for a friend of mine” he started to explain. “It has to be quite sexy, but not too revealing, cause she isn’t really fond of that. But it shouldn’t be too tame, it has to attract attention.” “I think I have the perfect dress for your friend!” the saleswoman said enthusiastically. “Let me find it for you.” And she was gone.

When she came back, she was carrying 3 dresses, and she started showing them to Oliver. “This first one is very popular in the club scene, and is very sexy, but it is also modest because of the top line that is quite high, and not too revealing.” She said. Oliver immediately saw that it was way too short for Felicity to feel comfortable in, so that one was off the table.  
“This one is also modest, and very sweet, if a dress can be called that..” the woman started, but Oliver interrupted. “This one is way too modest, though it is very beautiful, but it is not suited for the occasion.”   
“Well, then I have this third dress, which is a different sort of dress. The sleeves are made of see through lace, and the pattern of the lace continues on the bodice. The skirt is short, but not too short, and the belt around the middle brings an extra edge to it.” “It’s perfect..” Oliver breathed, glad he had finally found a dress which was suited for the occasion, and a dress which he was almost certain Felicity would approve of.   
“Thank you so much for your help” he told the saleswoman. He was so relieved to be done shopping, he almost ran out of the store after paying for the dress. 

OQOQOQOQOQOQ

When he got back to Verdant, Felicity and Digg were waiting for him so they could talk the mission through one more time. Felicity almost ran to him to find out what sort of dress he had bought. When he showed her, she said: “Oliver, that dress is perfect! I love it. It is sexy, yet elegant. I probably couldn’t have done better myself. Thank you.” She looked up at him with bright eyes. “How can I thank you?” She asked.   
“Seeing you in this dress will be thanks enough” he thought to himself. But to Felicity he said:”Let me take you to dinner once, sometime next week maybe? When we have finished this mission, and have some free time.” “I’d love to” Felicity told him, in an unintentional whisper. She was surprised at Oliver’s behaviour; he had never seemed interested in her, even told her in not so many words once, after having slept with Isabel. But she wouldn’t complain, she’d love to go to dinner with Oliver, he was one of her best friends, and even though she knew it was never going to go anywhere, she still loved spending time with him.  
Both of them had forgotten Digg was still in the room while they were having their whispered conversation. He didn’t mind though, he was still expecting something to happen soon, and it seemed like this dress buying Oliver had done had started the ball rolling.

**Notes for the Chapter:**

> Dresses which were shown to Oliver:  
> 1: http://www.dhgate.com/product/whloesale-20sde-1-pcs-elegant-dress-sexy/142114493.html  
> 2: http://lindadress.blogspot.nl/2011/12/black-chiffon-bridesmaid-dresses-knee.html  
> 3: http://www.fansshare.com/gallery/photos/10967374/new-fashion-women-elegant-vintage-sexy-lace-chiffon-pleated-dress-casual-slim-casual/?displaying


End file.
